Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 10.7, Problem 23ATS

(a)

Interpretation Introduction

Interpretation:

The selective reagents used to accomplish the given transformation should be draw and identified.

Concept Introduction:

Role of sodium amide: The strong base of NaNH2/NH3 will deprotonate alkynes, alcohols and other organic functional groups with acidic protons such as esters and ketones. It is also a very strong nucleophile. It is a strong base and excellent nucleophile. It’s used deprotonated of weak acids and also for elimination reaction.

Anti-Markovnikov addition: These rules describe the regioselectivity (particular place in functional group) where the substituent is bonded to a less substituted carbon, rather than the more substituted carbon. This placed is quite unusual as carbon cations which are commonly formed during alkene or alkyne reactions tend to favor the more substituted carbon.

Reduction property of 9-BBN: This reagent selectively reduced for carbon-carbon triple bond converted into bouble bond. The hydrogen ends up bond to the most substituted carbon and the stereo chemistry of the reaction is syn both new bonds are formed on the same face of the alkene.

(b)

Interpretation Introduction

Interpretation:

The selective reagents used to accomplish the given transformation should be draw and identified.

Concept Introduction:

Role of sodium amide: The strong base of NaNH2/NH3 will deprotonate alkynes, alcohols and other organic functional groups with acidic protons such as esters and ketones. It is also a very strong nucleophile. It is a strong base and excellent nucleophile. It’s used deprotonated of weak acids and also for elimination reaction.

Anti-Markovnikov addition: These rules describe the regioselectivity (particular place in functional group) where the substituent is bonded to a less substituted carbon, rather than the more substituted carbon. This placed is quite unusual as carbon cations which are commonly formed during alkene or alkyne reactions tend to favor the more substituted carbon.

Reduction property of 9-BBN: This reagent selectively reduced for carbon-carbon triple bond converted into bouble bond. The hydrogen ends up bond to the most substituted carbon and the stereo chemistry of the reaction is syn both new bonds are formed on the same face of the alkene.

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Organic Chemistry

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